US11793075B2 - Plurality of host materials and organic electroluminescent device comprising the same - Google Patents

Plurality of host materials and organic electroluminescent device comprising the same Download PDF

Info

Publication number
US11793075B2
US11793075B2 US16/908,973 US202016908973A US11793075B2 US 11793075 B2 US11793075 B2 US 11793075B2 US 202016908973 A US202016908973 A US 202016908973A US 11793075 B2 US11793075 B2 US 11793075B2
Authority
US
United States
Prior art keywords
substituted
unsubstituted
membered
alkyl
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active, expires
Application number
US16/908,973
Other languages
English (en)
Other versions
US20210013427A1 (en
Inventor
Bitnari Kim
Su-Hyun Lee
Doo-Hyeon Moon
So-Young Jung
Du-Yong Park
Hae-Yeon Kim
Sang-Hee Cho
Jin-Ri Hong
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Electronic Materials Korea Ltd
Original Assignee
Rohm and Haas Electronic Materials Korea Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020200066488A external-priority patent/KR20210006283A/ko
Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Publication of US20210013427A1 publication Critical patent/US20210013427A1/en
Assigned to ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD. reassignment ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHO, SANG-HEE, HONG, Jin-Ri, JUNG, SO-YOUNG, KIM, BITNARI, KIM, HAE-YEON, LEE, SU-HYUN, MOON, DOO-HYEON, PARK, Du-Yong
Application granted granted Critical
Publication of US11793075B2 publication Critical patent/US11793075B2/en
Active legal-status Critical Current
Adjusted expiration legal-status Critical

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same.
  • An electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • the most important factor determining luminous efficiency in an organic EL device is light-emitting materials.
  • the light-emitting materials are required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, and uniformity and stability of the formed light-emitting material layer.
  • the light-emitting material is classified into a host material and a dopant material in a functional aspect. In order to improve color purity, luminous efficiency and stability, a host and a dopant can be mixed and used.
  • the preferable characteristics of a host material should have high purity and a suitable molecular weight in order to be deposited under vacuum.
  • a host material is required to have high glass transition temperature and pyrolysis temperature to achieve thermal stability, high electrochemical stability to achieve long lifespan, easy formability of an amorphous thin film, good adhesion with adjacent layers, and no movement between layers.
  • the selection of the host materials is important since the host materials greatly affect the efficiency and lifespan of the light-emitting device.
  • KR 2019-0013353 A discloses an organic optoelectronic device using a compound having benzonaphtho-based heteroaryl moiety as a basic skeleton with a compound having carbazole-carbazole moiety, as a host of a light-emitting layer.
  • the prior art does not disclose a plurality of host materials using phenanthro-based heteroaryl moiety as a basic skeleton the same as the present disclosure.
  • the object of the present disclosure is firstly, to provide a plurality of host materials which are able to produce an organic electroluminescent device having high power efficiency, and/or long lifespan, and secondly, to provide an organic electroluminescent device comprising the host materials.
  • the present inventors found that the aforementioned objective can be achieved by a plurality of host materials comprising a first host material comprising a compound represented by the following formula 1 and a second host material comprising a compound represented by the following formula 2, so that the present invention was completed.
  • Y 1 represents O, S, CR 11 R 12 , or NR 13 ;
  • R 11 to R 13 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 11 and R 12 may be linked to each other to form a ring;
  • R 1 to R 3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted (C
  • R 13 , R 2 , and R 3 represent(s) -L 1 -(Ar 1 ) d ;
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • Ar 1 each independently represent(s) a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one nitrogen (N);
  • a and c each independently represent an integer of 1 to 4, b and d represent an integer of 1 or 2; and
  • each R 1 , each R 2 , each R 3 , and each Ar 1 may be the same or different,
  • X 21 and Y 21 each independently represent —N ⁇ , —NR 24 —, —O—, or —S—, provided that one of X 21 and Y 21 represents —N ⁇ , and the other represents —NR 24 —, —O—, or —S—;
  • R 21 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
  • R 22 to R 24 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)aryl
  • R 22 and R 23 represent(s) -L 21 -Ar 21 ;
  • L 21 represents a single bond or a substituted or unsubstituted (C6-C30)arylene
  • Ar 21 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted fused ring of (C3-C30)aliphatic ring and (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino;
  • f represents an integer of 1 or 2
  • g represents an integer of 1 to 4
  • each R 22 and each R 23 may be the same or different.
  • an organic electroluminescent device having high power efficiency and/or long lifespan can be prepared.
  • the present disclosure relates to a plurality of host materials comprising at least one first host material(s) comprising a compound represented by the above formula 1 and at least one second host material(s) comprising a compound represented by the above formula 2, and an organic electroluminescent device comprising the host materials.
  • organic electroluminescent material means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
  • the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (containing host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.
  • a plurality of host materials means a host material comprising a combination of at least two compounds, which may be comprised in any light-emitting layer constituting an organic electroluminescent device. It may mean both a material before being comprised in an organic electroluminescent device (e.g., before vapor deposition) and a material after being comprised in an organic electroluminescent device (e.g., after vapor deposition).
  • a plurality of host materials of the present disclosure may be a combination of at least two host materials, and selectively, conventional materials comprised in organic electroluminescent materials may be additionally comprised.
  • the at least two compounds comprised in the plurality of host materials of the present disclosure may be comprised together in one light-emitting layer, or may each be comprised in separate light-emitting layers by a method known in the field.
  • the at least two compounds may be mixture-evaporated or co-evaporated, or may be individually evaporated.
  • hole transport zone means a region in which holes move between a first electrode and a light-emitting layer and may include, for example, at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer.
  • the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer can be a single layer or a multi-layer of which two or more layers are stacked.
  • the hole transport zone may comprise a first and a second hole transport layers.
  • the second hole transport layer may be at least one layer of a plurality of transport layers, and further include one or more layers of a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer.
  • the hole transport zone may comprise a first and a second hole transport layers.
  • the first hole transport layer may be placed between a first electrode and a light-emitting layer
  • the second hole transport layer may be placed between a first hole transport layer and a light-emitting layer.
  • the second hole transport layer may be a layer serving as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer, and/or an electron blocking layer.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10.
  • the above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tent-butyl, etc.
  • (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7.
  • the above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (C3-C30)cycloalkenyl is meant to be a mono- or polycyclic hydrocarbon having a 3 to 30 carbon atom ring backbone, which has a double bond(s), in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7.
  • the above cycloalkenyl may include cyclopropenyl, cyclobutenyl, cyclopentenyl, etc.
  • (3- to 7-membered)heterocycloalkyl is a cycloalkyl having 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may comprise a spiro structure.
  • aryl specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthyl phenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, di benzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl,
  • the aryl may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 4′-methylbiphenyl, 4′′-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, p-terphenyl-4-
  • (3- to 30-membered)heteroaryl(ene) is an aryl having 3 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 25, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge.
  • the above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; and may be partially saturated.
  • the above heteroaryl may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s).
  • heteroaryl specifically may include a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridin
  • the heteroaryl may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridiny
  • fused ring of (C3-C30)aliphatic ring and (C6-C30)aromatic ring means a functional group of a ring in which at least one aliphatic ring having 3 to 30 ring backbone atoms, preferably 3 to 25, more preferably 3 to 18, and at least one aromatic ring having 6 to 30 ring backbone atoms, preferably 6 to 25, more preferably 6 to 18, are fused, e.g., a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane.
  • a carbon atom(s) of fused ring of (C3-C30)aliphatic ring and (C6-C30)aromatic ring may be replaced at least one heteroatom(s) selected from the group consisting of B, N, O, S, Si and P, preferably N, O and S.
  • heteroatom includes F, Cl, Br, and I.
  • Ortho position is a compound with substituents, which are adjacent to each other, e.g., at the 1 and 2 positions on benzene.
  • Meta position is the next substitution position of the immediately adjacent substitution position, e.g., a compound with substituents at the 1 and 3 positions on benzene.
  • Para position is the next substitution position of the meta position, e.g., a compound with substituents at the 1 and 4 positions on benzene.
  • a ring formed in link to an adjacent substituent means a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof, formed by linking or fusing two or more adjacent substituents; preferably, may be a substituted or unsubstituted (3- to 26-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof.
  • the formed ring may include at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably, N, O, and S. According to one embodiment of the present disclosure, the number of atoms of the ring skeleton is 5 to 20. According to another embodiment of the present disclosure, the number of atoms of the ring skeleton is 5 to 15.
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent.
  • the substituents may be a substituted or unsubstituted methyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstitute
  • a plurality of host materials according to one embodiment comprise a first host material comprising compound represented by the above formula 1 and a second host material comprising compound represented by the above formula 2; and the host material may be contained in the light-emitting layer of an organic electroluminescent device according to one embodiment.
  • the first host materials as the host material may comprise a compound represented by the following formula 1.
  • Y 1 represents O, S, CR 11 R 12 , or NR 13 ;
  • R 11 to R 13 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 11 and R 12 may be linked to each other to form a ring;
  • R 1 to R 3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted (C
  • R 13 , R 2 , and R 3 represent(s) -L 1 -(Ar 1 ) d ;
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • Ar 1 each independently represent(s) a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one nitrogen (N);
  • a and c each independently represent an integer of 1 to 4, b and d represent an integer of 1 or 2; and
  • each R 1 , each R 2 , each R 3 , and each Ar 1 may be the same or different.
  • Y 1 may be O, S, CR 11 R 12 , or NR 13 ;
  • R 11 and R 12 each independently may be a substituted or unsubstituted (C1-C30)alkyl or a substituted or unsubstituted (C6-C30)aryl; or may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, or aromatic ring;
  • R 13 may be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl, preferably, R 11 and R 12 each independently may be a substituted or unsubstituted (C1-C10)alkyl or a substituted or unsubstituted (C6-C18)aryl; or may be linked to each other to form a substituted or unsubstituted (5- to 30-membered
  • R 11 and R 12 each independently may be a substituted or unsubstituted (C1-C4)alkyl or a substituted or unsubstituted (C6-C12)aryl; or may be linked to each other to form a substituted or unsubstituted (5- to 25-membered) polycyclic aromatic ring;
  • R 13 may be a substituted or unsubstituted (C6-C18)aryl or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
  • R 11 and R 12 each independently may be a substituted or unsubstituted methyl, a substituted or unsubstituted phenyl; or may be linked to each other to form fluorene ring; and R 13 may be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted phenanthrenyl, or a substituted or unsubstituted dibenzothiophenyl.
  • R 1 and R 2 each independently may be hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, preferably, hydrogen, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl, more preferably, hydrogen, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl.
  • R 1 and R 2 each independently may be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted phenanthrenyl.
  • R 3 each independently may be hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, preferably, hydrogen, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl containing at least one nitrogen(s), more preferably, hydrogen, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl containing at least two nitrogens.
  • R 3 each independently may be hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinazolinyl, or a substituted or unsubstituted benzoquinazolinyl.
  • R 13 , R 2 , and R 3 represent(s) -L 1 -(Ar 1 ) d ; wherein L 1 may be a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; and Ar 1 may be each independently represent a substituted or unsubstituted nitrogen-containing (3- to 30-membered)heteroaryl containing at least one nitrogen(s).
  • At least one of R 13 and R 3 may be -L 1 -(Ar 1 ) d , preferably, R 3 may be -L 1 -(Ar 1 ) d .
  • L 1 may be a single bond or a substituted or unsubstituted (C6-C30)arylene, preferably, a single bond or a substituted or unsubstituted (C6-C25)arylene, more preferably, a single bond or a substituted or unsubstituted (C6-C18)arylene.
  • L 1 may be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted o-biphenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenylnaphthylene, or a substituted or unsubstituted phenanthrenylene.
  • Ar 1 each independently may be a substituted or unsubstituted nitrogen-containing (5- to 25-membered)heteroaryl containing at least one nitrogen(s), preferably, a substituted or unsubstituted nitrogen-containing (5- to 18-membered)heteroaryl containing at least two nitrogens.
  • Ar 1 each independently may be a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzoquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzoisoquinolyl, a substituted or unsub
  • Ar 1 may be at least one of a substituted or unsubstituted (C6-C30)aryl- and a substituted or unsubstituted (5- to 30-membered)heteroaryl-substituted or unsubstituted, triazinyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, or benzoquinoxalinyl.
  • the compound represented by formula 1 may be represented by any one of the following formulas 1-1 to 1-9.
  • Y 1 , L 1 , Ar 1 , R 1 to R 3 , and a to d are as defined in formula 1;
  • R 4 each independently is as defined as R 3 ;
  • each R 4 may be the same or different.
  • Y 1 may be O, S, CR 11 R 12 , or NR 13 ;
  • R 1 and R 2 each independently may be hydrogen, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
  • L 1 may be a single bond or a substituted or unsubstituted (C6-C30)arylene;
  • Ar 1 may be a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least two nitrogens; and d may be 1.
  • Y 1 may be O, S, CR 11 R 12 , or NR 13 ; R 1 and R 2 may be all hydrogen; L 1 may be a single bond or a substituted or unsubstituted (C6-C30)arylene; Ar 1 may be a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least two nitrogens; and d may be 1.
  • the first host material may be illustrated by the following compounds, but is not limited thereto.
  • the compound represented by formula 1 according to the present disclosure may be synthesized as represented by the following reaction schemes 1 to 4, but is not limited thereto; and may be produced by a synthetic method known to a person skilled in the art.
  • exemplary synthesis examples of the compounds represented by formula 1, specifically formulas 1-1 to 1-9 are described, but they are based on Suzuki cross-coupling reaction, Wittig reaction, Miyaura borylation reaction, Ullmann reaction, Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN 1 substitution reaction, SN 2 substitution reaction, and Phosphine-mediated reductive cyclization reaction, etc. It will be understood by one skilled in the art that the above reaction proceeds even if other substituents defined in the formulas 1-1 to 1-9 other than the substituents described in the specific synthesis examples, are bonded.
  • the second host materials as another host material may comprise a compound represented by the following formula 2.
  • X 21 and Y 21 each independently represent —N ⁇ , —NR 24 —, —O—, or, —S—, provided that one of X 21 and Y 21 represents —N ⁇ , and the other represents —NR 24 —, —O—, or, —S—;
  • R 21 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
  • R 22 to R 24 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)aryl
  • R 22 and R 23 represent(s) -L 21 -Ar 21 ;
  • L 21 represents a single bond or a substituted or unsubstituted (C6-C30)arylene
  • Ar 21 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted fused ring of (C3-C30)aliphatic ring and (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino;
  • f represents an integer of 1 or 2
  • g represents an integer of 1 to 4
  • each R 22 and each R 23 may be the same or different.
  • Y 21 when X 21 is —N ⁇ , Y 21 may be —O— or —S—; when Y 21 is —N ⁇ , X 21 may be —O— or —S—.
  • L 21 may be a single bond or a substituted or unsubstituted (C6-C25)arylene, preferably, a single bond or a substituted or unsubstituted (C6-C18)arylene.
  • L 21 may be a single bond or a substituted or unsubstituted phenylene, or a substituted or unsubstituted naphthylene.
  • Ar 21 may be a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, preferably, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C5-C25)aliphatic ring and (C6-C25)aromatic ring,
  • Ar 21 may be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstit
  • R 21 may be a substituted or unsubstituted (C6-C30)aryl, preferably, a substituted or unsubstituted (C6-C25)aryl, more preferably, a substituted or unsubstituted (C6-C18)aryl.
  • R 21 may be a substituted or unsubstituted phenyl or a substituted or unsubstituted p-biphenyl.
  • R 22 to R 24 each independently may be hydrogen, deuterium, halogen, or cyano, preferably, hydrogen or deuterium.
  • R 22 to R 24 may be all hydrogen.
  • the compound represented by formula 2 may be represented by any one of the following formulas 2-1 to 2-5.
  • X 21 , Y 21 , L 21 , Ar 21 , R 21 to R 23 , f, and g are as defined in formula 2;
  • R 25 and R 26 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)aryl
  • g′ represents an integer of 1 or 2
  • h and i each independently represent an integer of 1 to 3
  • i′ represents an integer of 1 to 4;
  • each R 23 , each R 25 , and each R 26 may be the same or different.
  • one of X 21 and Y 21 may be —N ⁇ , the other of X 21 and Y 21 may be —O— or —S—;
  • L 21 may be a single bond or a substituted or unsubstituted (C6-C30)arylene;
  • Ar 21 may be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted di(C6-C30)arylamino;
  • R 21 may be a substituted or unsubstituted (C6-C30)aryl; and R 22 to R 24 may be all hydrogen.
  • the second host material may be illustrated by the following compounds, but is not limited thereto.
  • the compound of formula 2 according to the present disclosure may be produced by synthetic method known to a person skilled in the art, in specific, may be used synthetic methods disclosed in a number of patent documents.
  • the compound of formula 2 may be synthesized by referring to the disclosed method in KR 2017-0022865 A (Mar. 2, 2017), but is not limited thereto.
  • the present disclosure provides the organic electroluminescent compound represented by the following formula 3-1.
  • X 21 , Y 21 , R 21 to R 23 , R 26 , f, g′, and i′ are as defined in formulas 2-1 to 2-5;
  • L 21 represents a single bond or a substituted or unsubstituted (C6-C30)arylene
  • R 31 and R 32 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; provided that, at least one of R 31 and R 32 represent(s) a substituted or unsubstituted (3- to 30-membered)heteroaryl.
  • Y 21 when X 21 is —N ⁇ , Y 21 may be —O— or —S—, preferably, X 21 may be —N ⁇ , and Y 21 may be —O—.
  • L 21 may be a single bond or a substituted or unsubstituted (C6-C25)arylene, preferably, a single bond or a substituted or unsubstituted (C6-C18)arylene.
  • L 21 may be a single bond or a substituted or unsubstituted phenylene, or a substituted or unsubstituted naphthylene.
  • R 31 and R 32 each independently may be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5- to 30-membered)heteroaryl, preferably, a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (5- to 25-membered)heteroaryl, more preferably, a substituted or unsubstituted (C6-C18)aryl or a substituted or unsubstituted (5- to 18-membered)heteroaryl.
  • R 31 and R 32 represent(s) a substituted or unsubstituted (3- to 30-membered)heteroaryl, e.g., R 31 and R 32 may be all a substituted or unsubstituted (3- to 30-membered)heteroaryl.
  • R 31 and R 32 each independently may be a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted benzonaphthofuranyl.
  • the organic electroluminescent compound represented by formula 3-1 may be more specifically illustrated by the following compounds, but is not limited thereto.
  • the organic electroluminescent device may comprise a first electrode; a second electrode; and at least one organic layer(s) between the first and second electrodes.
  • a first host material comprising a compound represented by formula 1 and a second host material comprising a compound represented by formula 2 may be included in the same organic layer or may be included in the different organic layers, respectively.
  • the organic layer may comprise at least one light-emitting layer, and the light-emitting layer may comprise at least one first host material comprising a compound represented by formula 1 and at least one second host material comprising a compound represented by formula 2, or may comprise the organic electroluminescent compound represented by formula 3-1 as a sole.
  • the light-emitting layer may comprise at least one compound(s) of compound C-1 to C-597 as a first host material represented by formula 1 and at least one compound(s) of compound H-1 to H-215 as a second host material represented by formula 2.
  • the organic layer may comprise the organic electroluminescent compound represented by formula 3-1.
  • the compound of formula 3-1 may be included as a light-emitting layer material, or a hole transport layer material among the hole transport zone, of the organic electroluminescent device.
  • first electrode and the second electrode may be an anode and the other may be a cathode.
  • first electrode and the second electrode may each be formed as a transmissive conductive material, a transflective conductive material, or a reflective conductive material.
  • the organic electroluminescent device may be a top emission type, a bottom emission type, or a both-sides emission type according to the kinds of the material forming the first electrode and the second electrode.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.
  • the organic layer may further comprise an amine-based compound and/or an azine-based compound other than the light-emitting material according to the present disclosure.
  • the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting layer, the light-emitting auxiliary layer, or the electron blocking layer may contain the amine-based compound, e.g., an arylamine-based compound and a styrylarylamine-based compound, etc., as a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting material, a light-emitting auxiliary material, or an electron blocking material.
  • the electron transport layer, the electron injection layer, the electron buffer layer, or the hole blocking layer may contain the azine-based compound as an electron transport material, an electron injection material, an electron buffer material, or a hole blocking material.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides, and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising such a metal.
  • a plurality of host materials according to one embodiment may be used as light-emitting materials for a white organic light-emitting device.
  • the white organic light-emitting device has suggested various structures such as a parallel side-by-side arrangement method, a stacking arrangement method, or CCM (color conversion material) method, etc., according to the arrangement of R (Red), G (Green), B (blue), or YG (yellowish green) light-emitting units.
  • a plurality of host materials according to one embodiment may also be applied to the organic electroluminescent device comprising a QD (quantum dot).
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer.
  • the hole injection layer may be multi-layers in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole injection layer may be doped as a p-dopant.
  • the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine the excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer to prevent a light-emitting leakage.
  • the hole transport layer or the electron blocking layer may be multi-layers, and wherein each layer may use a plurality of compounds.
  • An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode.
  • the electron buffer layer may be multi-layers in order to control the injection of the electron and improve the interfacial properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole blocking layer or the electron transport layer may also be multi-layers, wherein each layer may use a plurality of compounds.
  • the electron injection layer may be doped as an n-dopant.
  • the light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or the hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or the electron transport, or for preventing the overflow of holes.
  • the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or the hole injection rate), thereby enabling the charge balance to be controlled.
  • the hole transport layer which is further included, may be used as the hole auxiliary layer or the electron blocking layer.
  • the light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • a surface layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer
  • a surface layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer
  • a chalcogenide (including oxides) layer of silicon and aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a halogenated metal layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • the operation stability for the organic electroluminescent device may be obtained by the surface layer.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the halogenated metal includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds
  • the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • the light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi-layer of which two or more layers are stacked.
  • the light-emitting layer may further comprise one more dopant, and the doping concentration of the dopant compound with respect to the host compound of the light-emitting layer may be less than 20 wt %, preferably may be less than 10 wt %.
  • the dopant comprised in the organic electroluminescent material of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant.
  • the phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be preferably a metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an ortho-metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compound(s).
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • a thin film may be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent may be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • the first and second host materials may be used by the methods listed above, preferably, co-evaporation or mixture-evaporation.
  • the co-deposition is a mixed deposition method in which two or more isomer materials are put into respective individual crucible sources and a current is applied to both cells simultaneously to evaporate the materials and to perform mixed deposition; and the mixed deposition is a mixed deposition method in which two or more isomer materials are mixed in one crucible source before deposition, and then a current is applied to one cell to evaporate the materials.
  • each of the two host materials may be deposited individually.
  • the second host material may be deposited after the first host material is deposited.
  • the present disclosure can provide display devices such as smartphones, tablets, notebooks, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting, by using a plurality of host materials comprising the compound represented by formula 1 and the compound represented by formula 2.
  • OLEDs comprising the compounds according to the present disclosure were produced.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subject to an ultrasonic washing with acetone, trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 ⁇ 6 torr.
  • compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: The first and the second host materials of the following Table 1 were introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-39 was introduced into another cell as a dopant.
  • the two host materials were evaporated at a rate of 1:1 and simultaneously, the dopant was deposited in a doping amount of 3 wt % to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • compounds ET-1 and EI-1 were evaporated at a rate of 1:1, and were deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
  • an OLED was produced.
  • OLED was produced in the same manner as in Device Example 1, except that a second hole transport layer having a thickness of 45 nm is deposited using compound HT-3, and an electron blocking layer having a thickness of 15 nm was deposited using compound EB-1 on the second hole transport layer.
  • OLEDs were produced in the same manner as in Device Example 1, except that the compounds of the following Table 1 were used as the host of the light-emitting layer.
  • the organic electroluminescent device comprising a specific combination of compounds according to the present disclosure as a host material can show equal or higher efficiency and improved lifespan, compared with the organic electroluminescent device using a single host material (Device Comparative Examples 1 and 2) or using host materials in combination with a conventional host compound (Device Comparative Examples 3 and 4).
  • OLEDs according to the present disclosure were produced.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone and isopropylalcohol, sequentially, and then was stored in isopropylalcohol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • compound HI-3 was introduced into a cell of the vacuum vapor deposition apparatus, and compound HT-1 was introduced into another cell.
  • compound HI-3 was doped in a doping amount of 3 wt % with respect to the total amount of compounds HI-3 and HT-1 to form a hole injection layer having a thickness of 10 nm.
  • compound HT-1 was deposited to form a first hole transport layer having a thickness of 80 nm on the hole injection layer.
  • compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was then deposited thereon as follows:
  • the first the second host materials listed the following Table 3 were introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-39 was introduced into another cell as a dopant.
  • the two host materials were evaporated at a rate of 1:1 and simultaneously, the dopant was deposited in a doping amount of 3 wt % to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • compounds ET-1 and EI-1 as electron transport materials were deposited in a weight ratio of 50:50 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • OLED was produced in the same manner as in Device Example 4, except that the compound of the following Table 3 was used as the host of the light-emitting layer.
  • the organic electroluminescent device comprising a specific combination of compounds according to the present disclosure as host materials has improved with respect to driving voltage, luminous efficiency, and/or lifespan characteristics.
  • OLED according to the present disclosure was produced.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subject to an ultrasonic washing with acetone and isopropylalcohol, sequentially, and then was stored in isopropylalcohol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • fdsf compound HT-1 was introduced into another cell.
  • compound HI-3 was doped in a doping amount of 3 wt % with respect to the total amount of compounds HI-3 and HT-1 to form a hole injection layer having a thickness of 10 nm.
  • compound HT-1 was deposited to form a first hole transport layer having a thickness of 80 nm on the hole injection layer.
  • compound H-221 was introduced into another cell of the vacuum vapor deposition apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was then deposited thereon as follows: Compound RH was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-39 was introduced into another cell as a dopant. The two materials were evaporated at a different rate and deposited in a doping amount of 3 wt %, respectively, to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Next, compounds ET-1 and EI-1 as electron transport materials were deposited in a weight ratio of 50:50 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • OLED was produced in the same manner as in Device Example 11, except that the compound H-179 was used as the second hole transport layer material.
  • the organic electroluminescent device comprising an organic electroluminescent compound according to the present disclosure as a hole transport layer material has improved with respect to driving voltage, luminous efficiency, and/or lifespan characteristics.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
US16/908,973 2019-07-08 2020-06-23 Plurality of host materials and organic electroluminescent device comprising the same Active 2041-10-07 US11793075B2 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
KR10-2019-0082067 2019-07-08
KR20190082067 2019-07-08
KR10-2020-0003574 2020-01-10
KR20200003574 2020-01-10
KR10-2020-0066488 2020-06-02
KR1020200066488A KR20210006283A (ko) 2019-07-08 2020-06-02 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자

Publications (2)

Publication Number Publication Date
US20210013427A1 US20210013427A1 (en) 2021-01-14
US11793075B2 true US11793075B2 (en) 2023-10-17

Family

ID=74006092

Family Applications (1)

Application Number Title Priority Date Filing Date
US16/908,973 Active 2041-10-07 US11793075B2 (en) 2019-07-08 2020-06-23 Plurality of host materials and organic electroluminescent device comprising the same

Country Status (4)

Country Link
US (1) US11793075B2 (ja)
JP (1) JP2021013018A (ja)
CN (1) CN112201758B (ja)
DE (1) DE102020117804A1 (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114975839B (zh) * 2022-07-26 2022-10-28 吉林奥来德光电材料股份有限公司 一种有机电致发光器件、有机电致发光装置及光电设备

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108329272A (zh) * 2018-04-04 2018-07-27 长春海谱润斯科技有限公司 一种含芘结构的有机电致发光材料及其有机发光器件
KR20190013353A (ko) 2017-08-01 2019-02-11 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치
US20190214572A1 (en) * 2016-09-29 2019-07-11 Rohm And Haas Electronic Materials Korea Ltd Organic electroluminescent device comprising electrontransport layer and electron buffer layer

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130121479A (ko) * 2012-04-27 2013-11-06 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102456076B1 (ko) * 2015-09-03 2022-10-19 삼성디스플레이 주식회사 화합물 및 이를 포함하는 유기 발광 소자
WO2018159964A1 (en) * 2017-02-28 2018-09-07 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190214572A1 (en) * 2016-09-29 2019-07-11 Rohm And Haas Electronic Materials Korea Ltd Organic electroluminescent device comprising electrontransport layer and electron buffer layer
KR20190013353A (ko) 2017-08-01 2019-02-11 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치
CN108329272A (zh) * 2018-04-04 2018-07-27 长春海谱润斯科技有限公司 一种含芘结构的有机电致发光材料及其有机发光器件

Also Published As

Publication number Publication date
US20210013427A1 (en) 2021-01-14
CN112201758B (zh) 2024-08-09
CN112201758A (zh) 2021-01-08
DE102020117804A1 (de) 2021-01-14
JP2021013018A (ja) 2021-02-04

Similar Documents

Publication Publication Date Title
US11552257B2 (en) Plurality of host materials and organic electroluminescent device comprising the same
US20220045281A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US12096687B2 (en) Plurality of light-emitting materials, organic electroluminescent compound, and organic electroluminescent device comprising the same
US20210202849A1 (en) Plurality of host materials and organic electroluminescent device comprising the same
US20210184133A1 (en) Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same
US20210320263A1 (en) Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same
US12004420B2 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20220263031A1 (en) Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same
US20220069228A1 (en) Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same
US20240101892A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20220123230A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20220173322A1 (en) Organic electroluminescent compound, a plurality of host materials comprising the same, and organic electroluminescent device
US20220052271A1 (en) A plurality of host materials and organic electroluminescent device comprising the same
US20240260466A1 (en) Plurality of host materials and organic electroluminescent device comprising the same
US20220033414A1 (en) Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same
US20210376240A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20210305519A1 (en) Plurality of host materials and organic electroluminescent device comprising the same
US20210119142A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US11793075B2 (en) Plurality of host materials and organic electroluminescent device comprising the same
US20230157165A1 (en) Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same
US20230126428A1 (en) Plurality of host materials and organic electroluminescent device comprising the same
US20230117383A1 (en) Plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same
US20220048886A1 (en) Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same
US20220144855A1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
US20220102645A1 (en) Plurality of host materials and organic electroluminescent device comprising the same

Legal Events

Date Code Title Description
FEPP Fee payment procedure

Free format text: ENTITY STATUS SET TO UNDISCOUNTED (ORIGINAL EVENT CODE: BIG.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION

STPP Information on status: patent application and granting procedure in general

Free format text: NON FINAL ACTION MAILED

AS Assignment

Owner name: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD., KOREA, REPUBLIC OF

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KIM, BITNARI;LEE, SU-HYUN;MOON, DOO-HYEON;AND OTHERS;REEL/FRAME:064108/0184

Effective date: 20200603

STPP Information on status: patent application and granting procedure in general

Free format text: PUBLICATIONS -- ISSUE FEE PAYMENT RECEIVED

STPP Information on status: patent application and granting procedure in general

Free format text: PUBLICATIONS -- ISSUE FEE PAYMENT VERIFIED

STCF Information on status: patent grant

Free format text: PATENTED CASE